2,5-Dimethoxy-4-ethoxyamphetamine

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MEM's dose as 20 to 50mg orally and its duration as 10 to 14hours. Its effects have been reported to include color enhancement, visual phenomena, and pattern movement, among others.

Interactions

Pharmacology

Pharmacodynamics

MEM is a serotonergic psychedelic and acts as a selective serotonin 5-HT2 receptor agonist. It is specifically a full agonist of the serotonin 5-HT2A and 5-HT2C receptors and to a lesser extent is a partial to full agonist of the serotonin 5-HT2B receptor. The psychedelic effects of MEM are thought to be mediated by serotonin 5-HT2A receptor activation.

Chemistry

MEM, also known as 2,5-dimethoxy-4-ethoxyamphetamine, is a phenethylamine, amphetamine, and DOx derivative. It is the analogue and derivative of 2,4,5-trimethoxyamphetamine (TMA-2) in which a 4-ethoxy group is present instead of a 4-methoxy group.

Synthesis

The chemical synthesis of MEM has been described.

Derivatives

A variety of derivatives of MEM have been developed and studied, for instance by Daniel Trachsel and colleagues. These include MPM, MIPM, MALM, MMALM, MFEM, MDFEM, and MTFEM, among others.

History

MEM was first synthesized by Alexander Shulgin. It was first described by him in the scientific literature by 1968. Subsequently, Shulgin described MEM in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Society and culture

Legal status

Canada

MEM is a controlled substance in Canada.

United States

MEM is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

References

1. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology.
2. (28 March 2025). "Kᵢ Database".
3. Liu, Tiqing. "BindingDB BDBM50005255 (+/-)2-(4-Ethoxy-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::2-(4-Ethoxy-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL8225".
4. (February 2010). "Psychedelics and the human receptorome". PLOS ONE.
5. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun.
6. (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch Pharmacol.
7. (2023). "Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors". Front Pharmacol.
8. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug Alcohol Depend.
9. (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Front Pharmacol.
10. (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal.
11. (1991). "Pihkal: A Chemical Love Story". Transform Press.
12. (January 1968). "The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine". J Med Chem.
13. "Controlled Drugs and Substances Act".
14. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.